I am looking for approximately $30,000 to $35,000 to cover all repairs/expenses.

Especially in Florida when every year (almost) they suffer this kind of threats.As a flipper its very hard to find insurance company that will be ready to cover your house.As a home owner for rental: How much will the insurance company will cover in case of total disaster like this?

My realtor recommended a guy to me, but he injured his shoulder and can't get through a hatch to see the roof.

Hi BiggerPockets Community -I'm currently taking on a flip that's going to need some repair on the roof (specifically the truss) due to some fire damage prior to the acquisition.

Can anyone recommend an investor friendly real estate agent that covers the Brantford ON community? 

Around an 8.25 CAP, big value-add property which renovations/parking lot/covered parking etc...In my experience - you need to find an agent or broker to work with who is well connected in that asset class and can bring you deals.

Roofs, siding and a large deck needing repairs on the bigger rental.

When were the roof and HVAC last replaced?

The other option is to do a non agency product, such 12 months average bank deposits or asset depletion or DSC (debt service concerage) where 90% of the rent covers your total monthly payment 

You should consult with an SEC attorney and for your non-accredited investors, I would still structure it as closely as possible as you would for accredited just so that you have sound terms and all the legalities covered.